Hydrogen chloride-ethyl acetate → HCID 118622780, compound

HRID 2202320Notes

Reaction equation

HRID 2202320 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:15][C:16]([C@H:18]2[C:27]3[C:22](=[CH:23][C:24]([O:28][CH3:29])=[CH:25][CH:26]=3)[CH2:21][CH2:20][N:19]2C(OC(C)(C)C)=O)=[O:17])[CH:5]=[C:6]([F:14])[C:7]=1[C:8]([CH3:13])([CH3:12])[CH2:9][O:10][CH3:11].[ClH:37].C(OCC)(=O)C>C(OCC)(=O)C>[ClH:37].[F:1][C:2]1[CH:3]=[C:4]([NH:15][C:16]([C@H:18]2[C:27]3[C:22](=[CH:23][C:24]([O:28][CH3:29])=[CH:25][CH:26]=3)[CH2:21][CH2:20][NH:19]2)=[O:17])[CH:5]=[C:6]([F:14])[C:7]=1[C:8]([CH3:12])([CH3:13])[CH2:9][O:10][CH3:11]

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 131735759HCID 131735759, compound

Product 1

HCID 118622780HCID 118622780, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl (R)-1-((3,5-difluoro-4-(1-methoxy-2-methylpropan-2-yl)phenyl)carbamoyl)-6-methoxy-3,4-dihydroisoquinoline-2(1H)-carboxylate (200 mg, 0.40 mmol) in ethyl acetate (3 mL) was added 4M hydrogen chloride/ethyl acetate (4 mL) at room temperature, and the mixture was stirred overnight. The reaction mixture was concentrated under reduced pressure to give (R)—N-(3,5-difluoro-4-(1-methoxy-2-methylpropan-2-yl)phenyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline-1-carboxamide hydrochloride (175 mg, 0.397 mmol, 100%) as white crystals.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9489ed3447914905965808ecb3989263
Source dataset
uspto-grants-2016_06
Patent number
US09365520B2

Reaction notes

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